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Deoxyfluorination of Carboxylic Acids with CpFluor: Access to Acyl Fluorides and Amides

Xiu Wang, Fei Wang, Fengfeng Huang, Chuanfa Ni and Jinbo Hu*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China, Email: jinbohusioc.ac.cn

X. Wang, F. Wang, F. Huang, C. Ni, J. Hu, Org. Lett., 2021, 23, 1764-1768.

DOI: 10.1021/acs.orglett.1c00190


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Abstract

3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), a bench-stable fluorination reagent, can be used for an efficient deoxyfluorination of (hetero)aryl, alkyl, alkenyl, and alkynyl carboxylic acids to the corresponding acyl fluorides under neutral conditions. A synthesis of acyl fluorides with in-situ formed CpFluor, as well as a one-pot amidation reaction are also described.


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Key Words

acyl fluorides


ID: J54-Y2021